Chemistry of Heterocyclic Compounds: Pyridazines, Volume 28 PDF
Preview Chemistry of Heterocyclic Compounds: Pyridazines, Volume 28
PYR IDAZINES This is the twnty-eighth volume in the series THE CHEMISTRY OF HETEROCYCLIC COMPOUNDS THE CHEMISTRY OF HETEROCYCLIC COMPOUNDS A SERIES OF MONOGRAPHS ARNOLD WEISSBERGER and EDWARD C. TAYLOR Editors PYRIDAZINES Edited by Raymond N. Castle Department of Chemistry Brigham Young Uniuersity Provo. Utah AN INTERSCIENCE@P UBLICATION JOHN WILEY & SONS NEW YORK * LONDON * SYDNEY * TORONTO Copyright 0 1973, by John Wiley & Sons, Inc. All rights reserved. Published simultaneously in Canada. No part of this book may be reproduced by any means, nor transmitted, nor translated into a machine language with- out the written permission of the publisher. Library of Congress Cataloging in Publication Data: Castle, Raymond Nielson, 1916- Pyridazines. (The Chemistry of heterocyclic compounds, v. 28) Includes bibliographical references. 1. Pyridazine. 1. Title. [DNLM: 1. Pyridazines. QD 401 C353p 19731 QD401. C343 547'.593 72-13270 ISBN 0-471-38213-2 Contributors Anne G. Lenhert, Department of Chemistry, Kansas State Unioersity, Man- hattan, Kansas Raymond N. Castle, Department of Chemistry, Brigham Young University, Provo, Utah James W. Mason, Philco-Ford Corporation, Newport Beach, California Duane L. Aldous, College of Pharmacy, Xavier University of Louisiana, New Orleans, Louisiana Takenari Nakagome, Sumitomo Chemical Co., Ltd., 2-1, 4 Chome, Takat- sukasa, Takarazuka-shi, Hyogo-ken, Japan Takanobu Itai, Showa College of Pharmaceutical Sciences, Tokyo, Japan M. T i h , Department of Chemistry, University of Ljubljana, Ljubljana, Yugoslavia B. Stanovnik, Department of Chemistry, University of Ljubljana, Ljubljana, Yugoslav ia The Chemistry of Heterocyclic Compounds The chemistry of heterocyclic compounds is one of the most complex branches of organic chemistry. It is equally interesting for its theoretical implications, for the diversity of its synthetic procedures, and for the physio- logical and industrial significance of heterocyclic compounds. A field of such importance and intrinsic difficulty should be made as readily accessible as possible, and the lack of a modern detailed and compre- hensive presentation of heterocyclic chemistry is therefore keenly felt. It is the intention of the present series to fill this gap by expert presentations of the various branches of heterocyclic chemistry. The subdivisions have been designed to cover the field in its entirety by monographs which reflect the importance and the interrelations of the various compounds, and accommo- date the specific interests of the authors. In order to continue to make heterocyclic chemistry as readily accessible as possible, new editions are planned for those areas where the respective volumes in the first edition have become obsolete by overwhelming progress. If, however, the changes are not too great so that the first editions can be brought up-to-date by supplementary volumes, supplements to the respec- tive volumes will be published in the first edition. ARNOLDW EISSBERGER Research Laboratories Eastman Kodak Company Rochester, New York EDWARDC . TAYLOR Princeton University Princeton, New Jersey vii This book attempts to cover all the literature references on pyridazines from the earliest references through those references appearing in Chemical Abstracts to mid-1971. There is some deviation in individual chapters by the different authors. Some authors have added selected' references past mid- 1971. We have attempted at least to list in the tables all the pyridazines known during the period covered. There are some differences in style in the different chapters, reflecting different approaches taken by the individual authors. We trust that this volume will prove readable and useful to those engaged in research or development on the many phases of pyridazine chemistry. We also are hopeful that reading this volume may stimulate additional research in this simple heterocyclic ring system. Reference is made in this volume to very few condensed pyridazines. This forms the basis for a companion volume in this series, namely, Condensed Pyridazines Including Cinnolines and Phthalazines. We hope that these two volumes will be used together and serve as a starting point for research in these areas. RAYMONND. CASTLE Prouo, Utah July 1972 Contents I. Physical Properties of Pyridazines . . 1 ANNE G. LENHERTD, epartment of Chemistry, Kansas State University, Manhattan, Kansas RAYMOND N. CASTLED, epartment of Chemistry, Brigham Young University, Provo, Utah 11. The Pyridazinones, Alkoxy- and Aryloxypyridazines, and Related Compounds . . 23 JAMES w. MASONP, hilco-Ford Corporation, Newport Beach, California DUANE L. ALDOUSC, ollege of Pharmacy, Xavier University of Louisiana, New Orleans, Louisiana 111. Halopyridazines . . 219 DUANE L. ALDOUSC, ollege of Pharmacy, Xavier University of Louisiana, New Orleans, Louisiana RAYMOND N. CASTLED, epartment of Chemistry, Brigham Young University, Provo, Utah . IV. Pyridazine Aldehydes, Ketones, and Alcohols . 353 ANNE G. LENHERTD, epartment of Chemistry, Kansas State University, Manhattan, Kansas RAYMOND N. CASTLED, epartment of Chemistry, Brigham Young University, Provo, Utah . . V. Pyridazinecarboxylic Acids 407 JAMES W. MASONP, hilco-Ford Corporation, Newport Beach, California xii Contents VI. Aminopyridazines . . 463 TAKENARI NAKAGOME, Sumitomo Chemical Company, Ltd., Takatsukasa, Takarazuka-shi, Hyogo-ken, Japan VII. Nitropyridazines and Their Reduction Products (except Amines) . . 629 TAKENARI NAKAGOME, Sumitomo Chemical Company, Ltd., Takatsukasa, Takarazuka-shi, Hyogo-ken, Japan VILI. Pyridazine N-Oxides . . 675 TAKANOBU ITAI,S howa College of Pharmaceutical Sciences, Tokyo, Japan IX. Sulfur Compounds of Pyridazines . . 755 M. TI~LER,D epartment of Chemistry, University of Ljubljana, Ljubljana, Yugoslavia B. STANOVNDIKe,p artment of Chemistry, University of Ljubljana, Ljubljana, Yugoslavia . . Author Index 839 Subject Index . 1 2 3 4 5 6 7 8 9 0 PYRIDAZINES This is the twenty-eighth volrtme in the series THE CHEMISTRY OF HETEROCYCLIC C0,MPOUNDS
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